First asymmetric synthesis of a differentially silyl-protected tris(alkynyl)methyl methyl ether |
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Authors: | Convertino Vito Manini Peter Schweizer W Bernd Diederich François |
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Affiliation: | Laboratorium für Organische Chemie, ETH-H?nggerberg, CH-8093 Zürich, Switzerland. |
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Abstract: | For an improved synthesis of the recently described expanded octamethoxycubane with a central C56 core, formally obtained by inserting buta-1,3-diynediyl moieties into all C(sp3)-C(sp3) bonds of octamethoxycubane, the preparation of the optically pure methyl ether of a differentially silyl-protected trispropargylic alcohol was required. The key step of the preparation involved a diastereoselective addition of a lithium acetylide to an optically active alkynyl ketone under Cram chelation control. |
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